2-amino-4-hydroxy-6-omega-carboxytrihydroxy-propylpteridines



Patented Sept. 18, 1951 i l HYDliQXY-dOMEGA-CARBOXY- rainrpaoxvmaornrrizammns Harold- G. Petering 'and John A. Schmitt, Kala- Mich; assi norsto'rhe pany, "Kilamazbo; Mich a; corporation 013.4; 1

: a Michigan.

No Drawing. Application lil .r-i

Serial No. ria ira Thi invention relates to 2-amino-4-hydroxy- 6-omega carboxytrihydroxy propylpteridines having the formula:

HzNf N\ N T j-(CHOH) -COOH H wherein the polyhydroxy carboxylic acid side chain is attached to the pteridine ring in the 6 or 7 position and to their preparation.

The products of this invention are brown to tan solids, soluble in aqueous alkalies and acids, sparingly soluble in Water and relatively insoluble in most common organic solvents. They char and decompose without definite melting above 300 degrees centigrade and are best characterized by their ultra violet absorption spectra and the ratio of their extinction coefiicients at the absorption maxima. The purity of the product (freedom from the isomeric compound) can be ascertained by the numerical value of the extinction coefficient 257 mu 370 mu when determined in 0.1 normal alkali. When the is between about 2.9 and 3.2 the product is predominately the 6-isomer with the value of 3.3 connoting analytically pure 6-isomer. When the numerical value of the 370 mu ratio is about 2.3-2.5 the product is predominately the 7-isomer with the value 2.3 denoting pure 7-isomer. These products are useful as intermediates in the preparation of other chem- 4 Claims. (Cl. 260-2515) reaction mixtures-trawli rile product thus obtained can be separated from other than isomeric impurities by washing-"with water and organic solvents. Separation of the 6- and 7- isomers is accomplished by extraction with warm dilute ammonium hydroxide solution at pH 8-8.5 or boiling dilute acetic acid solution having a pH of about 6.

Example 1 A dry mixture was prepared containing 0.5 gram of 2,4,5-triamino-6-hydroxy pyrimidine dihydrochloride, 0.4 gram of sodium bicarbonate and 1.04 grams of calcium 5-keto gluconate. Six milliliters of water was added whereupon carbon dioxide was evolved. After the evolution of carbon dioxide had ceased 0.25 milliliter of glacial acetic acid and 0.28 milliliter of percent hydrazine hydrate solution were added to the reaction mixture. The mixture was placed on a steam bath where, as the temperature rose all of the solids went into solution resulting in a clear, light yellow solution. The reaction temperature was allowed to rise to about degrees centigrade where it was maintained for about 45 minutes. During this time the light yellow color of the reaction mixture deepened. became orange and finally a reddish-brown. At theend of the heating period the reaction mixture was cooled and the precipitate which separated was collected, washed successively with water, methanol and ether and dried. There was obtained 0.46 gram of 2-amino-4-hydroxyfi-omega carboxy trihydroxypropylpteridine (seventy percent of theoretical) whose ratio as determined in 0.1 normal sodium hydroxide solution was 3.2.

Example 2 257 mu 370 mu synapse 4 as determined in 0.1 normal sodium hydroxide 3. A compound represented by the formula: solution was 2.7. N N

Having thu described our invention, we claim: mNf (CHOEPCOOH 1. A member of the group of compounds N represented by the formula: 5

N N rim-f n N (CHOHh'COOH 4. The process comprising heating in acid 7 solution 2,4,5-tri-amino-6-hydro ypy midine and H 10 a member of the group consisting of 5-keto gluconic acid and galacturonic acid in the presence wherein the trihydroxypropylcarboxylic acid of hydrazine and isolatin the 2-amino-4- radical is attached to the pteridine ring-in a hydroxy-G (D-omega carboxy trihydrcxypropylmember of the group consisting of the 6- and pteridine from the reaction mixture. 7-positions. l6 I HAROLD G. PETERING.

2. A compound represented by the formula: JOHN A. SCHMITI.

HaN N N\ v No references cited.

r N iononn-coon 2o 

1. A MEMBER OF THE GROUP OF COMPOUNDS REPRESENTED BY THE FORMULA: 